This invention relates to N-(5-substituted pyrimidin-2-ylaminocarbonyl)sulfonamides and their use as agricultural chemicals.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR1## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR2## wherein R is butyl, phenyl or ##STR3## R.sub.1 is hydrogen or methyl. When tested for hypoglyemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR4##
Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides. ##STR5## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sup.1 is H, Cl, F, Br, NO.sub.2, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA1 R.sup.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.2 -C.sub.3 haloalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 -CH(CH.sub.3)OR.sup.5 or (CH.sub.2).sub.m OR.sup.5 where m is 1, 2 or 3; PA1 R.sub.a.sup.2 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl or OCH.sub.3 ; PA1 R.sub.b.sup.2 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl or R.sub.a.sup.2 and R.sub.b.sup.2 can be taken together to form --CH.sub.2 --.sub.5, --CH.sub.2 --.sub.4 or --CH.sub.2 CH.sub.2 -O-CH.sub.2 CH.sub.2 --; PA1 R.sub.c.sup.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; PA1 R.sup.3 is C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ; PA1 R.sup.4 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.5 is C.sub.1 -C.sub.3 alkyl; PA1 (1) when R.sub.a.sup.2 is OCH.sub.3, then R.sub.b.sup.2 is CH.sub.3 ; PA1 (2) when R.sup.3 is OCH.sub.3, then R.sup.4 is CH.sub.3 ; and PA1 (3) when R is Cl, then Y is F. PA1 (1) those compounds of Formula I, wherein R is CO.sub.2 R.sup.2 or SO.sub.2 NR.sub.3 R.sub.4. PA1 (2) those compounds of Formula I, wherein R.sup.1 is H. PA1 (3) those compounds of Preferred (1) wherein R.sup.1 is H. PA1 (4) those compounds of the More Preferred (3) wherein R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.2 -C.sub.3 haloalkyl, and Y is F, Cl, Br, CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CH.sub.2 Cl, and at least one of X or Z is CH.sub.3, OCH.sub.3, Et or OEt. PA1 (5) those compounds of the More Preferred (4), wherein X is H, CH.sub.3 or OCH.sub.3 and Y is F, Cl, Br, CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CH.sub.2 Cl. PA1 Methyl 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate; PA1 Methyl 2-{[(4-chloro-6-methoxy-5-methylpyrimidin-2-yl)-aminocarbonyl]aminosulfony l}benzoate; PA1 Methyl 2-[[[4-chloro-5-(2-chloroethyl)-6-methylpyrimidin-2-yl]aminocarbonyl]amino sulfonyl]benzoate; PA1 Methyl 2-[[(4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate; PA1 Methyl 2-[[(5-iodo-4,6-dimethylpyridimin-2-yl)aminocarbonyl]aminosulfonyl]benzoat e; PA1 Methyl 2-[[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzo ate; PA1 Methyl 2-[[(5-bromo-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoa te; PA1 Methyl 2-[[(5-ethyl-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoa te; PA1 2-Chloro-N-[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]benzenesul fonamide; PA1 Methyl 2-[[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]ben zoate; PA1 (2-Propenyl) 2-[[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)aminocarbonyl[aminosulfonyl]benz oate; PA1 Methyl 2-[[(5-chloro-4-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate; and PA1 Methyl 2-[[(5-ethyl-4-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974). ##STR6## wherein R is pyridyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds.